WO2000040668A1 - Materiau electroluminescent organique et element electroluminescent organique contenant ce materiau - Google Patents

Materiau electroluminescent organique et element electroluminescent organique contenant ce materiau Download PDF

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Publication number
WO2000040668A1
WO2000040668A1 PCT/JP2000/000022 JP0000022W WO0040668A1 WO 2000040668 A1 WO2000040668 A1 WO 2000040668A1 JP 0000022 W JP0000022 W JP 0000022W WO 0040668 A1 WO0040668 A1 WO 0040668A1
Authority
WO
WIPO (PCT)
Prior art keywords
organic electroluminescent
derivatives
organic
derivative
emitting layer
Prior art date
Application number
PCT/JP2000/000022
Other languages
English (en)
Japanese (ja)
Inventor
Tadao Nakaya
Takao Yamauchi
Takanori Konishi
Keisuke Yamamoto
Original Assignee
Taiho Industries Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP11002566A external-priority patent/JP2000204363A/ja
Priority claimed from JP11065198A external-priority patent/JP2000260568A/ja
Application filed by Taiho Industries Co., Ltd. filed Critical Taiho Industries Co., Ltd.
Priority to AU18908/00A priority Critical patent/AU1890800A/en
Publication of WO2000040668A1 publication Critical patent/WO2000040668A1/fr

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Classifications

    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3

Definitions

  • the present invention relates to an organic electroluminescence (EL) material and an organic EL device using the same, and more particularly to a novel organic material emitting red light and an organic EL device using the same.
  • EL organic electroluminescence
  • an EL device using an organic compound has, as a basic structure, a light-emitting layer of an organic compound and a pair of counter electrodes sandwiching the light-emitting layer from above and below.
  • light emission when an electric field is applied between the two electrodes, electrons are injected from the cathode side, holes are injected from the anode, and the electrons recombine with holes in the light emitting layer, resulting in an energy level. Is a phenomenon in which energy is emitted as light when returning from the conduction band to the valence band.
  • the basic configuration of an organic EL device known today has a layered structure in which an anode 2, a hole transport layer 3, a light emitting layer 4, and a cathode 6 are sequentially stacked on a substrate 1, as shown in Fig. 2.
  • a cathode 6 has a simple metal such as aluminum (A 1), magnesium (M g), indium (In), silver (A g), or A 1—M g, A g ⁇ Alloys of these metals, such as Mg and A1-Li, can be used that have low work functions.
  • the light-emitting layer 4 is made of an organic compound that emits fluorescence.
  • organic compound that emits fluorescence For example, conventionally, various compounds such as anthracene, naphthalene, phenanthrene, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, and coumarin derivative are used. Specifically, tris (8-quinolinol) aluminum bismuth (8-quinolinol) magnesium, tris (5-chloro-8_quinolinol) gallium, etc. are used. It had been.
  • Examples of the electron transporting layer 5 include fluorenone, anthraquinodimethane, diphenoquinone, [2- (4'-t-butylphenyl) -15- (biphenyl) -11,3,4-oxadiazol] and the like. .
  • a transparent conductive material having a large work function such as indium tin oxide (ITO) or tin oxide is used.
  • the substrate 1 only needs to have thermal and mechanical strength and be transparent.
  • a glass substrate or a highly transparent resin such as a polyethylene plate or a polypropylene plate can be used.
  • Each of these layers can be formed by applying an appropriate method such as vacuum evaporation, sputtering, and spin coating.
  • each layer is not particularly limited, but each layer must be set to an appropriate thickness. Generally, it is said that the thickness of each layer is preferably in the range of about 100 nra to 100 000 nm. If the thickness is too large, a high voltage is required to obtain a certain luminance, Efficiency decreases. In addition, the deterioration is accelerated by the high voltage, resulting in a disadvantage that the life is shortened. On the other hand, if the film thickness is too thin, sufficient light emission will occur even when an electric field is applied due to the generation of pinholes and the like. Not always.
  • the present inventors have disclosed in Japanese Patent Application Laid-Open No. 11-255700 an organic EL device using an acetylaceton-based metal complex for the light-emitting layer, and Japanese Patent Application Laid-Open No. 11-3200.
  • 97737 we proposed an organic EL device using a phorazole derivative for the hole transport layer, and obtained an organic EL device that emits yellow and green light.
  • An object of the present invention is to provide an organic electroluminescent material that emits red light and an organic EL device that emits red light.
  • the organic electroluminescent material according to the invention is a
  • the organic electroluminescent device comprises at least a substrate, a light emitting layer provided on the substrate, and a pair of opposed electrodes sandwiching the light emitting layer from above and below.
  • the light emitting layer is
  • R i and R 2 represent an aryl compound, at least one of which contains a conjugated double bond, and R 3 represents a phenyl group, a methyl group or a methoxy group.
  • the light emitting layer may include:
  • the organic EL material of the present invention exhibits a bright red emission color by containing the europium derivative.
  • this material as a light emitting layer, a bright red emission is obtained.
  • An EL element that emits color is obtained.
  • the present invention is characterized by providing a light-emitting layer that emits bright red light, and other substrates, holes, electron transport layers, and electrodes can use known materials. Detailed description of the drawings
  • FIG. 1 shows the Eu (DFP) 3 (Diphen) derivative synthesized in Examples of the present invention.
  • ⁇ -NMR (CDC 1 3) is a chart.
  • FIG. 2 is a cross-sectional view schematically showing a general structure of an organic EL device.
  • FIG. 3 is a cross-sectional view schematically showing a partially deformed structure of the organic EL device of FIG. BEST MODE FOR CARRYING OUT THE INVENTION
  • the present inventors have proposed an organic EL device using an acetylacetonate-based metal derivative as a light-emitting layer, as described above.
  • 1,3-diketon (; 8-diketon) compounds represented by acetylacetonate produce extremely stable chelates.
  • acetylacetone is Na, K , Ti, Au, A1, Mn, Cs and so on.
  • a derivative emitting fluorescence is obtained by introducing an atomic group having a specific structure into the ligand of the / 3-diketon, and by using this derivative as a light emitting layer, sufficient light emission can be obtained at a low voltage.
  • an organic EL device having a long lifetime was obtained (Japanese Patent Application Publication No. Hei 11-255570).
  • the emission color of this element is yellow or green, the present inventors have further studied and found that
  • An object of the present invention is to introduce an atomic group having a specific structure into the ligand of the Eu derivative (the above formula and R 2 ), and the basis thereof is to use an aryl compound having a conjugated double bond with a small number of ligands.
  • the introduction of a ligand having a conjugated double bond can provide an Eu derivative that emits an unprecedented red color.
  • R 3 represents a fuel group, a methyl group or a methoxy group.
  • aryl compound having a conjugated double bond one or two of a formula compound and a complex cyclic compound, that is, the same compound or a different compound may be used, but at least a compound having a conjugated double bond is introduced. It is necessary to.
  • the cyclic compound include benzene and its derivatives, naphthalene, anthracene, phenanthrene, pyrene, coronene and the like.
  • Complexes such as aromatic compounds having one or more benzene rings and derivatives thereof, conjugated compounds such as bifunyl and distyryl and derivatives thereof, furans, thiofurans, oxazols, thioxazols, kylobazols and derivatives thereof And cyclic compounds and derivatives thereof.
  • R 2 is In the case of, it emits red light.
  • the light emitting layer is made to contain two components of Eu derivative containing two kinds of ligands of —diketon derivative and phenanthroline derivative and Alq 3 represented by the following formula (2).
  • the emission luminance of the obtained EL device is improved as compared with the case of using the Eu derivative alone.
  • the emission luminance is higher than the other Ri and R 2 , and further R i and R 2 are In this case, the emission luminance is higher than that of the furan.
  • A1q3 has been conventionally used in the light-emitting layer of an organic EL device, and emits yellow-green to green light. If the Eu derivative is used in combination, the reason is unknown, but Thus, the yellow-green to green light emission of the Eu derivative is suppressed, and conversely, the red light emission luminance of the Eu derivative is increased.
  • Eu derivatives used in the present invention include:
  • the thickness of the light-emitting layer in the case of Eu derivatives alone, 200 to 1 000 A is rather good, the case of laminating the Eu derivative and A 1 q 3, film of Al q 3 relative to the thickness 200 to 700 A of Eu derivatives
  • the thickness should be 100-600A. Emission color of the original Al q 3 when the thickness of the A lq 3 increases than the (yellow-green-green) present -10-The red color of the Eu derivative changes, and it does not emit pure red light.
  • the film thickness is as in the case of Eu derivatives alone, it is preferably in the range of 2 00 ⁇ 1 000 A, mixing ratio is a preferred range is a lq 3 3 0 to 60 parts with respect to Eu derivative 1 00 parts of the Al q 3 has free than the above range, it tends to be rather pure red emission.
  • the present invention is characterized by providing a light emitting layer that emits red light in an organic EL device.
  • the substrate, the hole transport layer, the electron transport layer, the electrodes, and the like that constitute the device are characterized by the following: Known materials described in the art can be used.
  • Eu derivatives of the present invention alone, and the organic EL element elaborate viewing set of Eu derivatives and A lq 3 as a light-emitting layer exhibits a sufficient light emission at a low voltage of 1 to 2 V, the average life span is about 50,000 hours position, Extremely long.
  • ITO anode
  • TPD hole transport layer
  • Al-Li light-emitting layer
  • TPD hole transporting layer
  • Equation (10) The measurement results of the above three types of organic EL devices are as shown in Table 1, and the emission color of each device was true red. Voltage / Current density Luminance Emission color Peak wavelength Chromaticity (V, mA / cra "(cd / m" (DI) XY
  • R i franc 6 9 0 0 1 8 0 crimson 62 1 0. 63 0.35
  • R, phenyl
  • Anode (IT0), hole transport layer (TPD, 600 A), light-emitting layer (composition described in Table 2), and cathode (A1-Li, 2000 A)
  • Three kinds of organic EL devices having different light emitting layer compositions were manufactured by stacking. If the light-emitting layer is composed of Eu derivative thin film and Al q 3 thin film, are stacked Eu derivative Seiana ⁇ feed layer, then A lq 3, were laminated in this order of the cathode. If the light-emitting layer is composed of a mixture of Eu derivative and Alq 3, the mixing ratio of Eu derivative and A 1 q 3 was 1 00 parts to 3 0 parts.
  • a novel europium derivative alone, and a composition in which a europium derivative and Alq 3 are combined are used in a light emitting layer, thereby exhibiting high-luminance red light emission at low voltage, and An organic EL device having a long life can be obtained.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un élément électroluminescent organique qui devient rouge foncé lorsqu'il est placé dans un état luminescent. Cet élément comprend un substrat (1), une paire d'électrodes (2) et (6) formées sur ce dernier, et une couche luminescente (4) placée entre les électrodes. Ladite couche luminescente comprend un composé d'europium représenté par la formule (1). Dans cette dernière, R1 et R2 représentent chacun un composé allyle et chacun comprend au moins une double liaison conjuguée. R3 représente phényle, méthyle ou méthoxy et un Alq3 représenté par la formule (2).
PCT/JP2000/000022 1999-01-08 2000-01-06 Materiau electroluminescent organique et element electroluminescent organique contenant ce materiau WO2000040668A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18908/00A AU1890800A (en) 1999-01-08 2000-01-06 Organic electroluminescent material and organic electroluminescent element containing the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP11/2566 1999-01-08
JP11002566A JP2000204363A (ja) 1999-01-08 1999-01-08 有機エレクトロルミネッセンス材料及びそれを用いた有機エレクトロルミネッセンス素子
JP11065198A JP2000260568A (ja) 1999-03-11 1999-03-11 有機エレクトロルミネッセンス素子
JP11/65198 1999-03-11

Publications (1)

Publication Number Publication Date
WO2000040668A1 true WO2000040668A1 (fr) 2000-07-13

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WO (1) WO2000040668A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6844090B2 (en) 2001-09-06 2005-01-18 Lg Electronics Inc. Organic electroluminescent device

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10130639A (ja) * 1996-10-25 1998-05-19 Agency Of Ind Science & Technol メカノルミネッセンス材料
JPH10231476A (ja) * 1997-02-19 1998-09-02 Oki Electric Ind Co Ltd 有機ｅｌ素子

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10130639A (ja) * 1996-10-25 1998-05-19 Agency Of Ind Science & Technol メカノルミネッセンス材料
JPH10231476A (ja) * 1997-02-19 1998-09-02 Oki Electric Ind Co Ltd 有機ｅｌ素子

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6844090B2 (en) 2001-09-06 2005-01-18 Lg Electronics Inc. Organic electroluminescent device
US6984463B2 (en) 2001-09-06 2006-01-10 Lg Electronics Inc. Organic electroluminescent device

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Publication number Publication date
AU1890800A (en) 2000-07-24

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